Operation Flying Starfish
by TinkerbellReturns
Summary: Response to prompt: "Neal gives advice to Henry on his first date", by swanfirefamily. What Neal Cassidy hadn't actually expected was to go on a date as well, one that had so many chances of going wrong. Both father and son knew, after all, that Emma Swan was a tough cookie! The first part focuses on the father/son dynamic; the second half consists entirely of Swanfire fluff.


Neal Cassidy was in a hurry. His son was probably waiting for him at Granny's, and he couldn't risk ruining that day: Henry's first date! At least, the very first one he had been officially consulted about, as a father.

He was slightly out of breath when he turned one last corner and took the final couple of steps that separated him from the diner. The boy had finally gathered the nerve to approach his crush from school, and Neal had agreed to be around for "psychological support" – which only showed how little he actually knew about dating, for starters.

Who, in their right mind, would want their parents to be watching their first date?

His son, however, had taken remarkably well to the idea. He had the distinct impression that no matter how hard he tried to reassure Henry, he still felt slightly pessimistic about the outcome of that first romantic encounter, and what could provide more comfort than making a fool of himself knowing his father would be doing the same?

On a date.

With Emma Swan.

Worst case scenario, they would both laugh some time later at their double fiasco.

"Hey Ruby," he muttered, rushing to the counter as his eyes darted around until they spotted Henry sitting by the window. "Is everything ready?"

"It is," she replied with a smirk. "Though I have to say, the candied kumquats were a pain to find."

"Ruby, please, tell your grandma I will pay her for every second of her time, she jus-"

"She was not amused, I'll tell you this," the woman responded, her eyebrow going up as her grin widened. "But after she saw the last topping… I guess you won her over."

He cleared his throat. That last topping made his stomach flutter, as the threat of an even greater public fiasco stared at him in the face.

"She will not even charge you anymore."

"Oh no, Ruby, I… I insist."

"Well, you can insist later," she replied, reaching for a tray. "Henry's been waiting for you for quite some time."

"Oh, right…"

His eyes were once again on Henry, and a smile curled his lips. He had to tip his hat to the kid: his face was absolutely peaceful, as if he was just killing time in a café, bored to death, while waiting for a friend to join him. Nothing would have revealed his nervousness, had he not been shaking his leg on and off, just like Neal himself would do in such occasions.

"Hey buddy!" he said, taking a seat across from his son. "You ready?"

"Ready."

"Is she here already?" he whispered, leaning over the table as his eyes darted around the café.

"Yes," Henry replied, his gaze shifting to a group of very talkative girls sitting at a table at the other side of the lounge.

"What's her name again?"

"Grace."

Trying to be as discreet as he could, Neal turned his head to locate the girl.

"Nice name," he said, an instant before spotting the group. "Which one is she?"

"The one with dark blond hair… brown eyes. She's wearing a hat."

He fumbled with the scarf around his neck and turned to look at his son again.

"She is very pretty," he said, winking and making the boy's ears go even redder than they already were. "And she brought quite an army with her."

"Oh, they will all leave soon," Henry answered, with the knowledge of someone who had been watching the girl from a distance for the past couple of weeks. "But she always stays, waiting for her father."

"Oh, I see," Neal answered. "Then we have time to review a few things."

"Yup."

"Great…" he continued, a wide grin forming in his face as he prepared to give his son a last round of dating advice. "So, rule number one..."

"Pay attention to what she says."

"No."

"No?" Henry squeezed his eyes, as if searching his mind for the correct answer. "Oh wait. Try to look your best."

"Right. Not _the _best, but... your best. Wash your face, brush your teeth, fix your hair. Don't look like you've just woken up from a nap..."

"_...in the backseat of a bug_," Henry completed, nodding. "Got it."

"But don't overdo it," Neal continued, raising a finger. "You don't wanna end up looking like a dandy. You still have to be yourself."

"Ok."

He paused, and peeked under the table to check whether his son had fallen into the trap of wearing fancy shoes for a date - an awful idea, from his own experience. After Emma had complained his footwear was horribly outdated, he had decided to surprise her that afternoon with a shiny new pair of leather oxfords, only to find out they were uncomfortable as hell. His son, however, had outsmarted him yet again, and resorted to a good ol' pair of sneakers that matched his comfy jeans perfectly well.

"Ok, I see you got that covered. You feel good?"

"I guess," Henry said with a shrug.

"That's good. If you don't, you won't have a good time. Neither will she."

"Right."

Neal couldn't help but smile at all the trust in his son face. Should he remind the boy, again, that the last time he took a girl on a date it ended up with her trying to shoot him in the face some time later? Talk about a man with a poor dating history... But still, that was his role as a father: to support his son whenever the kid needed him to, even in missions like those, for which he felt he was so poorly-equipped.

"Ok, now back to what you said before," he continued. "Pay attention to her, to what she says. It's important. Write things down if you have to, especially if you have bad memory, like me."

He watched as Henry reached into his pocket before speaking again.

"I brought a notepad."

"Good idea. But hey, don't use it as you two talk, ok? You don't want her to think you're interviewing her," he said, with a smirk. "Or worse, that you're taking notes for some sort of secret operation."

"Hey!" Henry's face lit up when he heard that magic word. "We could call it Operation Starfish!"

"Starfish?"

"Yeah!"

"Why starfish?" Neal asked, frowning. The truth was that he never understood the logic behind the names his son had picked for their secret operations. The boy shrugged, and he ended up raising his eyebrows and pouting. "Then maybe we should go for... _Flying Starfish?_"

Now Henry was the one who looked positively confused.

"_Flying_ starfish?"

"Because we are both trying to accomplish the impossible?" Neal explained, and Henry blinked. What a horrible thing to tell his son on his first date, that he was doomed to fail in his gallant quest for teenage love! "I mean,_ I_ am, not you. _Me._ I have never been that popular with women, and your mother... well, she's a tough cookie."

Henry nodded solemnly at the truth contained in those words: if there was one thing they both knew very well, was that Emma Swan was, indeed, a tough cookie.

"Operation Flying Starfish it is," the boy finally replied.

"That settles it," Neal went on, once again fumbling with his scarf. "Now back to the notes. If she says something really important, like... her favorite candy, or color, or... I don't know, things she likes on her sundae... Take a few notes when she goes to the restroom, for example."

"Got it."

"You might want to have all that info for future reference. And Henry..."

His face was serious when he leaned over the table to look more closely at his son.

"Not all first dates end with a kiss, okay?" he said, noticing his son was blushing. "Take my first date with your mum, for example..."

"What happened?"

Neal shifted uncomfortably on his seat, pressing the tips of his fingers together as he wrinkled his forehead.

"Your mother, she..." he whispered, glancing over his shoulder to make sure they were not being heard. "She threw up on me."

"Eeeeww!"

"But Henry, listen, this is our secret, ok?" he said. "Your mother can never_, ever_ know I told you this, okay?"

"Okay," Henry replied, his face a mix of amusement and curiosity. "But... But how... How did she-"

"I took her out for a drink..." he whispered, scratching his nose as he revisited that day in Portland. "And well... She drank something she had never drunk before... I told her to take it easy, but she didn't..."

"What did she drink?"

He let out a chuckle, and cleared his throat before answering.

"A couple of bourbons. 'Til this day, she won't come any near a bottle without wincing."

The boy was now chuckling as well, looking much more relaxed than before.

"But in the end, it was still the best date of my life," he said, his eyes dreamy as he spoke. "Of course, I would change the grand finale if I was given the chance," he heard Henry laugh, and chuckled as well, "but the truth is that after that day, your mother and I became really, really good friends. And we would see each other every day, and laugh a lot, and talk... until one day…" he bit his lower lip, the memory of their first kiss flashing behind his eyes, "...it happened. So, regardless of what happens with Grace today, the important thing is that you two feel good about each other, even if it's just... talking and laughing," he fluffed the kid's hair with a proud smile on his lips. "You have nothing to be nervous about, ok?"

"Thanks, dad," Henry said, with a wide grin on his face, before his eyes darted to the back of the lounge.

Neal turned around to follow his gaze, and saw the group of girls stand up and get ready to leave, except for Grace, who remained seated and was waving her goodbyes.

"I think that's your cue," he whispered. "Good luck."

"For you too," Henry answered, as he got to his feet."Where's mum, by the way?"

"Must be on her way."

"Ok, then. Bye!"

He watched as his son drew in a long breath, looking hesitant for a moment before a smile curled his lips and he turned on his heels to walk towards Grace's table.

Neal took that chance to change places at the table, so that he had a better view of what was happening at the back of the lounge. Of course, he would not stare because it would surely make the two kids uncomfortable, but every now and then he would cast a glance towards them, just to see whether they were at least having a good time.

And judging by the smiles on the two kids' faces as they talked, things had started well.

"Sorry I'm late."

Not five minutes had passed when Emma joined him, taking off her hat and placing it on the table. "Family issues, as usual."

"You tell me…" he replied, his eyes darting from her face to the gloves she had just taken off.

"Have you seen Henry?" she asked, taking a seat across from him as she tucked a strand of hair behind her ear. "I haven't seen him all day."

He pointed towards the table where the boy was sitting with a slight nod, smiling, and Emma turned around to see what he was talking about.

"Is our son… on a date?" she asked, turning back to look at him after spotting Henry and Grace laughing over their hot cocoas.

"He is," Neal replied, raising his eyebrows as he fumbled with his scarf for the millionth time that afternoon. He now realized it had already become some sort of nervous tick he couldn't control, just like his leg shaking under the table.

"I think I know that girl…" she whispered, frowning, before turning around to look at the girl again. "Oh, I remember now!" she exclaimed, and her eyes were again on Neal's face. "She's Jefferson's daughter!"

"Jefferson?"

"The Mad Hatter."

"Oh…"

His eyebrows involuntarily went up, and he let out a very faint whistle while looking at his own hands.

"I don't even know why… for a moment, I thought she was just… _a girl._"

"Well…" Emma let out a sigh, "If there is one thing we both know now, is that things, and people, are hardly ever what they look like…"

And then her eyes pierced his, and he felt his throat tighten. There were so many things about their present and past that fit under that umbrella, most of them far from good…

What a great beginning to their date.

Trying to escape the temptation of calling the whole thing off and head home before Emma Swan mocked him for what he was about to do, his gaze went back to his son, and the knot on his throat seemed to loosen up a little. He was beaming, and so was the girl by his side.

When Henry's eyes caught his, Neal discreetly gave him the thumbs up, and the boy replied accordingly, an exchange that did not go unnoticed by Emma, who once again turned her head around.

"You are giving our son dating advice?" she asked, looking thoroughly amused.

"What?" he, on the other hand, tried to look as clueless as possible.

"You _are,_ aren't you?"

He wetted his lips and tried not to smile.

"My God, I hope you are not teaching him your pick-up lines..."

"What is wrong with my pick-up lines?"

"Really?" she asked, cocking her head to the side as she looked at him.

"Well... I did get the girl in the end, didn't I?"

"Despite your pick-up lines, yes."

"Oh, I know that," he answered, snickering as he crossed his arms over the table.

"What?"

"That you fell for me because of my… _fierce magnetism_," he said, watching her throw her head back, laughing. "Wonderful sense of humor… Inhumanly impressive good looks."

"And your modesty," she completed, her eyes smiling like the rest of her face when she spoke.

"_And _my modesty, yes."

Emma Swan wished she could understand why, out of all the men that had crossed her path, Neal Cassidy was the only one who managed to make her smile as if it was the most effortless task in the world. She wondered why, after eleven years of hurt, away from each other, with nothing but the bitter memory of an unexplained departure, they had caught up with each other's lives so fast… as if not a single day had gone by, as if they were both travelling around Oregon to rob convenience stores.

She wondered how, even now that their lives were so completely different, now that they were parents, now that they had reunited with their own parents, engaged in all sorts of unlikely adventures… they were still so close to each other, so aware of each other, so in love – despite an evil fiancée, a flirty pirate, a curse, a prophecy, a portal.

There were so many things that hurt when she thought about her past… about how things could have been different if Neal had looked for her at some point...

But it was useless.

They would never be able to go back in time and make amendments, and the only choice she could make now was whether she wanted or not to be with that man from now on, if she was willing to give him another chance, if she would be able to trust.

If only her heart hadn't jumped ahead and made that choice long before her mind engaged in such considerations.

"Really now," his voice broke her reverie for a moment. "When did it happen?"

"What?"

"What made you… fall for me?"

She let out a smile, looking at her own hands over the table as she shook her head. What a question. Neal had never been the archetypical Prince Charming, even when he was in his most gallant days. But there was something about him that drew her in, and maybe it was his relentless optimism back in the day, maybe it was his jokes, maybe it was the fact that he was struggling not to break as much as she was and still, his heart had always seemed untouched by all the crap life kept throwing at him. Maybe it was the way he smiled, maybe it was his eyes, maybe it was how whole-heartedly he seemed to kiss her, losing himself in her arms when they slept together, giving her his share of the food when their hauls were not particularly successful. Maybe it was his lack of patience fixing stuff, his pet peeves, his irritation when others made him waste his time, his bad taste for shoes, his strange obsession with scarves and hoods. Maybe it was just… because.

"Despair?" she replied, shrugging, without looking at him to see the shocked expression her response elicited.

"Whoa..."

"Alcohol?"

When she finally raised her eyes to his, she saw his jaw had dropped.

"I was not wearing my glasses?" she chuckled.

"Yes," he said, his eyes finally regaining some of the confidence her words seemed to shake a moment before, "you were."

"I don't know, Neal. I don't know when I fell for you."

"Oh come on," he insisted. "You _have_ to know."

"I don't, I…" she shrugged again, shaking her head. "I don't know."

"You wanna know when I fell for you?"

And then, he was giving her one of those looks that always made her feel like smiling.

"When I stole your car?"

"Well, yeah, that made quite a first impression, but…"

"But what?"

"That day… when we went to that ice-cream parlor in Eugene…"

She let her head fall onto her crossed arms over the table, and her shoulders shook with laughter.

"And it was like… this huge place," he laughed as well. "And we were broke… totally broke. Remember?"

She lifted her head again, and waited until her laughter subsided to speak again.

"I'll tell you ten things I want in my sundae…" she said.

"… and when we come back to this place, you have to order it," he completed.

"And you came up with all those stupid things…" Emma added, wiping away happy tears as she remembered how dumb the two of them looked as they strolled down the aisles filled with the most absurd ice cream flavors and toppings, their mouths gaping as if they were two children lost in Candyland. "Candied bacon… Salty black licorice…"

"And we went back… like, a month later, when we had finally scraped up the money."

"Yeah."

"And you remembered all of them... all the ten things I had chosen."

She stared into his eyes for a moment, amazed at how fond he seemed to be of that particular memory. All the little things… with them, nothing had ever needed to be epic.

_Their dreams had never been that big._

"You fell for me because of a sundae?" she asked, her voice quiet as she smiled.

"Well…" he replied, a sad smile curling his lips. "I fell for you because of a lot of things…"

She watched his face as his eyes dropped to the table, as if he was revisiting his own set of past plans and promises. Then he looked up at her for an instant, but his head quickly turned to face the counter and nod towards Ruby.

"But that day… yeah," he whispered. "I think that was when I realized it."

She cleared her throat, straightening her back when Ruby approached them.

"Here it is," the dark-haired woman said, grinning as she pulled out a little piece of paper from her pocket. "A special sundae, with hot pineapple sauce, lemon curd, fresh plums, candied kumquats, meringue, maple syrup, sautéed apples, almonds and toasted coconut," Ruby said, folding back the paper and winking at Neal before turning to leave. "Enjoy!"

"Thanks, Ruby."

That was the only thing she could mutter as she stared at the tub of ice cream in front of her.

_Stupid Neal Cassidy._

She felt her eyes prickle at the corners as she poked a piece of apple drizzling with maple syrup. _Stupid, stupid man._ She didn't want to feel like a teenager again. She didn't want to feel happy that he remembered.

"Where in Storybrooke did you find candied kumquats?" she asked, still staring at the tip of her spoon.

"All I know is that Granny was not amused."

"You don't wanna mess with Granny…" she muttered, smiling lightly as she spoke. "She has a crossbow."

She only raised her eyes from the sundae when she saw a second spoon poking a kumquat.

"What?" he asked when her eyes searched for his. "You weren't able to eat it all that day in Eugene, you won't be able to eat it all now."

"I can't believe you remembered all the toppings."

"Oh, I had to write them down that day," he said, before taking the spoon to his mouth. "But yeah, I kept the list… for a rainy day."

She shook her head when he winked, and kept trying to take a little bit of every single topping in her spoon.

"They were out of peanut butter pretzels," he said, scooping out more ice cream from the tub. "So I replaced it with something else, I hope you don't mind."

"If it is as good as the rest," she answered, happily munching on an almond. "I swear I won't be bothered."

She saw him swallow and raise his eyebrows, and couldn't help but laugh.

And then, the tip of her spoon poked something solid.

She lowered her head to inspect the ice cream, trying to uncover what the spoon had found.

"Aw hell no…" she whispered, her face going pale when her eyes finally made out the circular shape of a metallic object among the sauce, cream and fruit. "Neal?"

His eyes were darting from the ice cream to her face, and his lips seemed to twitch for a second.

"I think you found the tenth topping…"

She kept staring at the ring submerged in vanilla ice cream, her brain barely registering that she could have choked on it earlier on. Her spoon gently wiped away the messy concoction of creams that hid the silver surface from sight, but the very little she could see revealed it was encrusted with little dark opals all along its center.

She had never been a fan of diamonds, anyway, or any gemstones. Or jewelry, in general. But silver was nice. And she liked those stones, they reminded her of a party at the beach.

_Stupid Neal Cassidy._

"You like it?" he asked, as his eyes still darted from her face to the sundae.

"I… I…"

"Hmm?"

"Yes," she let out a smile, finally shifting her glance to his face. "Yes, I do, I… I like-what are you doing?"

Her eyes went wide when he took the ring in his spoon and led it to his mouth.

"Cleaning it."

Her jaw dropped to the ground.

"Oh my God," she muttered, embarrassment evident in her voice. "You see, this is why, _this is exactly why_ I worry about you giving our son dating advice."

"Why?"

"You were doing so well," she said, watching the ring poke out from between his lips, "But you always find something lame to do."

"It's not lame," he replied, as he held the ring between his teeth. "It's sexy."

"It's lame."

"Either way, you like it."

"Oh really?"

"You're smiling."

_Stupid Neal Cassidy._

"Come on," he said, leaning forward.

"Come on what?"

"Come get it."

She snorted, and tried to snatch the ring away from his mouth, but he was faster and turned his face away.

"Nah, don't ruin it," he whispered. "You know how to do it right."

"You have to be joking."

"People are looking."

For the first time, she became fully aware that at least half of the diner had their heads turned towards them, eyeing them both expectantly.

"Yes, they are," she snarled. "Happy now?"

"Not yet."

He tilted his head, wiggling his eyebrows invitingly.

"You know, one of us can end up swallowing that thing," she whispered.

"Worry not. I got that scenario covered as well."

"Of course you do..."

"Come on, Emma... When was the last time you made a fool of yourself?"

"Not that long ago, unfortunately."

"Still, I think it's time... to catch up with me."

That man and his ability to make a fool of himself and drag her along, as if it was actually something to be proud of. She would have a hell of a hard time getting the townsfolk's credibility again now that half of them were about to witness her doing something that idiotic.

"I can't believe I'm doing this," she whispered, before lifting herself slightly from the seat and leaning forward to place a hand behind his neck, bringing his mouth closer to hers and kissing him softly on the lips, long and deep enough to get a taste of pineapple on his tongue.

When she finally broke the kiss and leaned back, she took a moment to lower her head and touch her lips, her fingers grabbing the ring she had successfully captured. Smiling embarrassedly, she raised it so that their audience could see the evidence of her triumph, and the whole diner broke into a roar of applause and whistles.

"Don't even dare look that proud of yourself," she managed to complain, despite the happy smile on her face as he took the ring from her hand and placed it on her finger, squeezing her hand into his and bringing it to his lips for a soft kiss.

Proud, however, was not the best word to describe Neal Cassidy. A sweaty mess of wrecked nerves mixed with relief, joy and excitement would be a more appropriate description.

His eyes darted around the diner as people approached Emma to congratulate her, and his gaze finally fell upon the person he was looking for.

It was Henry's turn to give his father the thumbs up with a happy smile on his face, with an equally happy girl sitting by his side.

_Operation Flying Starfish had been a success._


End file.
